6-Bromonaphthalene-2-sulfonyl chloride → 1-(6-Bromonaphthalene-2-sulfonyl)-4-(4-diisopropylaminomethylbenzoyl)piperazine

HRID 278593Notes

Reaction equation

HRID 278593 reaction equation
[CH:1]([N:4]([CH2:8][C:9]1[CH:22]=[CH:21][C:12]([C:13]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])=[CH:11][CH:10]=1)[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([S:34](Cl)(=[O:36])=[O:35])[CH:28]=[CH:27]2>C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([S:34]([N:18]1[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C:12]3[CH:21]=[CH:22][C:9]([CH2:8][N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:2])[CH3:3])=[CH:10][CH:11]=3)[CH2:16][CH2:17]1)(=[O:36])=[O:35])[CH:28]=[CH:27]2

Participants

5

Reactant 2

HCID 144577416-Bromonaphthalene-2-sulfonyl chlorideHCID 226279521-(4-Diisopropylaminomethylbenzoyl)piperazine

Product 1

HCID 226279921-(6-Bromonaphthalene-2-sulfonyl)-4-(4-diisopropylaminomethylbenzoyl)piperazineYield 59.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 1-(4-diisopropylaminomethylbenzoyl)piperazine (200 mg) in 10% sodium hydrogen carbonate solution (10 ml) and ethyl acetate (15 ml), was added 6-bromonaphthalene-2-sulfonylchloride (179 mg), and the solution was stirred at room temperature for 30 minutes. The organic layer was separated, washed with water and extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution and extracted with dichloromethane. The extract was dried and concentrated. The residue was crystallized with ether to give the title compound (201 mg), as colorless crystals.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. extractionextracted with 1 N hydrochloric acid
  4. extractionextracted with dichloromethane
  5. customThe extract was dried
  6. concentrationconcentrated
  7. customThe residue was crystallized with ether

Sources & evidence

ORD record
ord-7207ae2e68a44ed68f7c777a00adbed8
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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